Synthesis of aryl 2‐(2‐imidazolyl)ethyl ketones | Zendy

Abdelaal Salma M. | Zendy; Kim JangWoo | Zendy; Bauer Ludwig | Zendy

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Synthesis of aryl 2‐(2‐imidazolyl)ethyl ketones

Author(s) -

Abdelaal Salma M.,

Kim JangWoo,

Bauer Ludwig

Publication year - 1995

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570320338

Subject(s) - chemistry , sodium borohydride , aryl , catalysis , medicinal chemistry , hydrolysis , platinum , organic chemistry , alkyl

The Claisen‐Schmidt condensation of 1‐(triphenylmethyl)‐2‐imidazolecarboxaldehyde with acetophenones yielded 1‐aryl‐3‐[1‐(triphenylmethyl)‐2‐imidazolyl]propen‐1‐ones 7 . Selective catalytic hydrogenation over platinum of 7 furnished 1‐aryl‐3‐(2‐imidazolyl)‐1‐propanones 8 . An alternate synthesis of 8 started with sodium borohydride reduction of 7 to give allylic alcohols, 1‐aryl‐3‐[1‐(triphenylmethyl)‐2‐imidazolyl]‐2‐propen‐1‐ols 10 , which were rearranged by hot aqueous sodium to 8 . Acid hydrolysis of 8 provided the title compounds and triphenylmethanol.

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